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Merck

M8699

(R)-MG132

≥98%, Proteasome inhibitor

(R)-MG132

Synonym(s):

Z-L-Leu-D-Leu-L-Leu-al

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About This Item

Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62
UNSPSC Code:
12352200
NACRES:
NA.32

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Product Name

(R)-MG132,

InChI

1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1

InChI key

TZYWCYJVHRLUCT-VABKMULXSA-N

SMILES string

CC(C)C[C@@H](C(N[C@H](C(N[C@H](C=O)CC(C)C)=O)CC(C)C)=O)NC(OCC1=CC=CC=C1)=O

assay

≥98%

solubility

DMSO or DMF: 25 mg/mL

storage temp.

−20°C

Quality Level

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1 of 4

This Item
SML1135L5793L8511
assay

≥98%

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥85% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO or DMF: 25 mg/mL

solubility

DMSO: soluble

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

Application

(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor.[1][2][3][4]

Biochem/physiol Actions

MG132 (carbobenzoxy-Leu-Leu-leucinal) is a tri-peptide aldehyde. It possesses antitumor activity and boosts cytostatic/cytotoxic effects of chemo- and radiotherapy.[5] (R)-MG132 is a potent, membrane-permeable proteasome inhibitor. It can inhibit proteasome activity in lysates of J558L multiple myeloma cells and EMT6 breast cancer cells. The (R)-MG132 stereoisomer is a more effective inhibitor of chymotrypsin-like (ChTL), trypsin-like (TL), and peptidylglutamyl peptide hydrolyzing proteasome (PGPH) activities than the (S)-MG132.[5]

Physical form

crystalline solid or supercooled liquid

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach.
Mroczkiewicz M, et al.
Journal of Medicinal Chemistry, 53(4), 1509-1518 (2010)
Alternative promotion and suppression of metastasis by JNK2 governed by its phosphorylation.
Hu S, et al.
Oncotarget, 8(34), 56569-56569 (2017)
Activation of anaphase-promoting complex by p53 induces a state of dormancy in cancer cells against chemotherapeutic stress.
Dai Y, et al.
Oncotarget, 7(18), 25478-25478 (2016)
Determination of H-ATPase Activity in Arabidopsis Guard Cell Protoplasts through H-pumping Measurement and H-ATPase Quantification.
Yamauchi S and Ken-ichiro S
Plant Physiology (2016)
A Mad2-Mediated Translational Regulatory Mechanism Promoting S-Phase Cyclin Synthesis Controls Origin Firing and Survival to Replication Stress.
Gay S, et al.
Molecular Cell, 70(4), 628-638 (2018)

Questions

1–2 of 2 Questions  
  1. What is the molarity of a solution with a concentration of 25 mg/ml in DMSO?

    1 answer
    1. The molarity of a 25 mg/ml solution is 0.052 M, which is equivalent to 52 mM. This calculation is based on a substance with a molar mass of 475.62 g/mol, where a 1 M solution is prepared by dissolving 475.62 g in 1 liter.

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  2. Which cells are utilized to assess the bioactivity of Product No. M8699, also known as (R)-MG132?

    1 answer
    1. The biological activity of product No. M8699, (R)-MG132 was measured using J558L multiple myeloma cells and EMT6 breast cancer cells.

      Helpful?

Reviews

Active Filters

  1. Newark. NJ, USA
    • Review 1
    • Vote 1
    5 out of 5 stars.

    Worked spot on!!!

    The product worked at 25micromolar concentration for rat neonatal myocytes

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